The dresses that made Anna Wintour fashion's #1

The Dress Files |
By Spencer Cain
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She's fashion's most powerful woman and was very possibly the inspiration behind Lauren Weisberger's The Devil Wears Prada. She is as famed for her sunglasses and razor-sharp bob as she is for her tenure at the helm of US Vogue – but how much do you really know about Anna Wintour? Ahead of her birthday on 3 November, we've compiled a list of the 11 dresses that make her a fashion icon (it was hard to narrow it down – trust) and accompanied 'em with facts bound to impress even the savviest of fash-fans.

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She was born into a media empire

Anna's dad, Charles Wintour, was a legendary editor of the Evening Standard, and her stepmother Audrey Slaughter launched magazines including Honey and Petticoat. Oh, and her lil' bro Patrick is a political reporter at The Guardian. Our guess is that the convos at the Wintour dinner table growing up were a little more intellectual than 'Pass the potatoes, plz'.

Anna Wintour at the PEN American Center Gala in honour of Arthur Miller, 1997

Picture: Getty

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The bob has been her 'do for 50 years

Fashions come and go, but one thing that has remained consistent for five decades is Anna's signature bob haircut. She first debuted it in the 60s as Vidal Sassoon was making the super-sleek look famous. But he never actually cut her hair, the hairdresser revealed in an interview in 2010. 'I would love to talk to her about it, but I can't just call and say "I love the way you're wearing my hair".'). During Fashion Month, Anna now keeps her locks immaculate with twice-daily blowouts.

Picture: Getty

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She was a total badass as a teen

It takes a serious #bawse to rule the hallways of the Condé Nast building with an iron fist, but don't think Anna is all bizness. She was a serious rebel in her secondary school days, saying 'Meh!' to dress codes and regularly altering her uniform to show a lil' more skin, according to Jerry Oppenheimer's biog of the lady in question, Front Row. Instead of staying at home hitting the books, she also became a fixture at London's hottest nightclubs, where the length of your hemline wasn't a concern.

Anna Wintour at the Awakenings film screening in New York City, 1990

Picture: Getty

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She's a shrewd political operator, too...

Anna is a famed supporter of the left-leaning Democrats and offered some unofficial wardrobe-based support to the then-First Lady, Hillary Clinton, in 1993 (and put her on a Vogue cover five years later). Rumours also abounded that Wintour was in the running for the role of US ambassador to London during Obama's administration, and just this week, Hillary and Anna were the subject of more speculation, after the two were spotted perusing racks of clothes at Michael Kors' studio.

Anna Wintour at the Bid for Love auction to benefit God's Love We Deliver, 1993

Picture: Getty

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11

Her love of tennis is second only to her love of fashion

Anna's passion for tennis is well-known: it extends from playing (she famously rises at 6am everyday to get in a game before work) and her friendships with champions (you can often spot her in the stands cheering on Roger Federer) to using it as an editorial theme – it's a leitmotif that makes regular appearances on the pages of Vogue.

Anna Wintour dancing in a silver gown with Oscar de la Renta, 1990s

Picture: Getty

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11

She and Kate Middleton have something in common

Aside from being British, of course: Anna and Kate both share a strong sense of loyalty when it comes to their footwear. For K-Middz, it's all about an LK Bennett nude pump, and for Anna, nothing but a Manolo Blahnik strappy sandal will do. Another accessory fact is that Wintour rarely carries a bag (one of many characteristics she shares with Miranda Priestly, editor of the fictional Runway magazine in The Devil Wears Prada).

Picture: Getty

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She has seriously green fingers

Gardening is another of Anna's greatest passions – her estate in Mastic, Long Island, is home to her prized gardens and she's not afraid to show them off. In fact, she recently hosted her son Charles' wedding in the stunning grounds. 'I can only hope my own Long Island gardens are as exquisite when my son, Charlie, gets married in June,' she wrote in her editor's letter.

Picture: Getty

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Timing is very important to Anna

If you want to be at the top of the fashion world like Anna, you've gotta bring your A-game – and that takes discipline. She may be photographed at a glitzy event every night, but she usually stays at a shindig for less than 20 minutes (no one wants to be the last one at the party, dahling). She's then in bed by 10.15pm and wakes promptly at 6am. Lateness is never an option. In fact, Marc Jacobs starts his runway shows on time at her request.

Anna Wintour at an event in a yellow dress, 1990s

Picture: Getty

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She's made plenty of enemies

When you're considered one of the most influential figures in your industry, haters are inevitable, and by far the biggest anti-Wintour crew is animal rights organisation PETA. She once wrote: 'I wear fur. I also eat juicy steaks.' Well, that resulted in a pie being thrown at her mink while she entered the Chloé runway show at Paris Fashion Week back in 2005. Undeterred, Anna is now accompanied by bodyguards when she attends shows, who also double up as her personal handlers. Literally.

Anna Wintour in red at an event at Barneys New York in New York City, 1999

Picture: Getty

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She's partly responsible for North West

When the media was buzzing with reports that Kim Kardashian and Kanye West were set to name their daughter North West, Anna encouraged them to do it. Kim was quoted in British GQ saying, 'She told us, "North is a genius name"'. Well, if it's good enough for Anna...

Anna Wintour in a mini silver dress at an event, 1990s

Picture: Getty

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Her staple piece will surprise you

Anna's most prized piece is not an item of clothing but her work desk. It was custom-designed for her by architect and designer Alan Buchsbaum (who also created interiors for the likes of Diane Keaton and Billy Joel), shortly before his death in 1987. Side note: it has no drawers. 'I like everything out in the open', Wintour once said. We like the way she thinks.

Anna Wintour at the Fresh Air Fund's Salute to American Heroes event, 1995